787618-22-8

Basic information

• Product Name: 2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I-PROPOXY-1,1'-BIPHENYL
• Synonyms: 2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl, min.98%;dicyclohexyl(2',6'-diisopropoxybiphenyl-2-yl)phosphine;{2-[2,6-bis(propan-2-yloxy)phenyl]phenyl}dicyclohexylphosphane;Dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine;98% RuPhos;2-DicyclohexylphosphiNA-2',6'-diisopropoxy-1,1'-biphenyl;2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl,RuPhos;2-Dicyclohexylphosphino-2',6'-di-i-propoxy-1,1'-biphenyl,98% RuPhos
• CAS NO: 787618-22-8
• Molecular Formula: C₃₀H₄₃O₂P
• Molecular Weight: 466.63
• EINECS: 1312995-182-4
• Product Categories: Achiral Phosphine;Aryl Phosphine;Buchwald Ligands Series;Buchwald Ligands&Precatalysts
• Mol File: 787618-22-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 123-124°C
• Boiling Point: 551.7 °C at 760 mmHg
• Flash Point: 360.7 °C
• Appearance: white/Powder
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I-PROPOXY-1,1'-BIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I-PROPOXY-1,1'-BIPHENYL(787618-22-8)
• EPA Substance Registry System: 2-DICYCLOHEXYLPHOSPHINO-2',6'-DI-I-PROPOXY-1,1'-BIPHENYL(787618-22-8)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 787618-22-8(Hazardous Substances Data)

Usage

Reaction

Versatile Ligand for the Pd-catalyzed coupling of secondary arylamines and alkylamines. Ligand used for the Pd-catalyzed Negishi cross-coupling reaction of (hetero)arylchlorides. Synthesis of ladder-type π-conjugated heteroacenes via palladium-catalyzed double N-arylation and intramolecular O-arylation. A palladium-catalyzed regiospecific synthesis of N-aryl benzimidazoles, Versatile ligand used for the Pd-catalyzed C-N coupling reaction of secondary aryl- and alkyl-amines at low temperature with the Pd precatalyst. Ligand used for the Pd-catalyzed Suzuki-Miyaura coupling of aryl chloride and NHC-boranes. Ligand for the palladium-catalyzed trifluoromethylation of hindered aryl chlorides. Ligand used for the palladium-catalyzed coupling of alkyl boronates.

Uses

Different sources of media describe the Uses of 787618-22-8 differently. You can refer to the following data:
1. suzuki reaction
2. 2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl is the ligand used for the palladium-catalyzed coupling of alkyl boronates.
3. Bulky phosphine ligand used in a palladium-catalyzed cross-coupling of aminoethyltrifluoroborate?s with electron-poor aryl bromides.

Upstream product

• 108-46-3 recorcinol 
• 79128-08-8 1,3-diisopropoxybenzene 
• 16523-54-9 chlorodicyclohexylphosphane 
• 870703-70-1 2-(2-bromophenyl)-1,3-diisopropyloxybenzene 

Downstream Products

• 1190363-46-2 (6S,9R)-6-(2,3-difluorophenyl)-9-((triisopropylsilyl)oxy)-6,7,8,9-tetrahydro-5Hcyclohepta[b]pyridin-5-one 
• 1287211-62-4 (η4-nornornadiene)Rh(2-(dicyclohexylphosphino)-2',6'-diisopropoxy-1,1'-biphenyl)Cl 
• 1028206-60-1 chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl)-palladium(II) 

Relevant articles and documents

Development of a scalable palladium-catalyzed α-arylation process for the synthesis of a CGRP antagonist

The Pd-catalyzed α-arylation of cycloheptapyridyl ketone is a key complexity-building step in the synthesis of BMS-846372, a CGRP antagonist. A first-generation process utilized Pd(OAc)2/PtBu 3·HBF4 catalyst system with a strong base NaO tBu. Although this process was demonstrated on multi-kilo scale, the harsh conditions led to non-selective metal catalyzed processes, which generated several operational, quality, and throughput issues. By acquiring detailed knowledge around several important process parameters, we were able to design an efficient and scalable second-generation α-arylation process using a Pd(OAc)2/RuPhos catalyst system with the weaker base, K 3PO4 in tert-amyl alcohol. This new weak base process was high yielding, efficient, and superior in several respects compared to the strong base process. The strategy behind the reaction and isolation development and the process considerations important to scaling a catalytic reaction from laboratory to manufacturing scale will be discussed.